ANISOLE 181 PREPARATION 77. Anisole (Methyl phenate, Phenyl methyl ether), CGH5.O.CH3 Cahours, A?malen^ 1851, 78, 226. 5 grms. sodium. 100 c.c. methyl alcohol, 20 grms. phenol. 40 „ methyl iodide. The methyl alcohol is poured into a round flask (250 c.c.) connected with an upright condenser. The sodium, cut into small pieces, is then added, the flask being detached from the condenser for 'a moment and replaced. When the sodium has dissolved, the phenol and methyl iodide are added. The mixture is heated on the water-bath until the solution has no longer an alkaline reaction (two to three hours). As much as possible of the methyl alcohol is distilled off on the water-bath and water added to the amber-coloured residue. A colourless oil separates out, which is extracted with ether. The ethereal solution is dehydrated over calcium chloride and distilled, first on the water-bath until the ether has been driven off, and then over the flame. Almost the whole of the residue distils at 150 — 155°. Yield, nearly theoretical. Properties. — Colourless liquid, possessing an agreeable smell ; b. p. 154° ; sp. gr. o'99i at 15°. See Appendix, p. 294. > PREPARATION 78. Hexahydrophenol (Cyclohexanol), C0H11.OH Sabatier and Senderens, Compt. rend.) 1901, 132, 210. 50 grms. phenol. The phenol is reduced with hydrogen in presence of finely divided metallic nickel ; which acts as a catalyst. The apparatus is shown in Fig. 79.